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WO2014120865A1 - Procédés de manipulation de composés chlorés utilisés dans la fabrication de hfo-1234yf - Google Patents

Procédés de manipulation de composés chlorés utilisés dans la fabrication de hfo-1234yf Download PDF

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Publication number
WO2014120865A1
WO2014120865A1 PCT/US2014/013742 US2014013742W WO2014120865A1 WO 2014120865 A1 WO2014120865 A1 WO 2014120865A1 US 2014013742 W US2014013742 W US 2014013742W WO 2014120865 A1 WO2014120865 A1 WO 2014120865A1
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WO
WIPO (PCT)
Prior art keywords
ppm
supply
reactive compound
reactive
compound includes
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/US2014/013742
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English (en)
Inventor
Selma Bektesevic
Haiyou Wang
Hsueh Sung Tung
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Honeywell International Inc
Original Assignee
Honeywell International Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Honeywell International Inc filed Critical Honeywell International Inc
Priority to EP14746383.0A priority Critical patent/EP2951124A4/fr
Priority to CN201480007302.XA priority patent/CN105026311A/zh
Priority to MX2015009943A priority patent/MX2015009943A/es
Priority to JP2015556121A priority patent/JP2016515069A/ja
Publication of WO2014120865A1 publication Critical patent/WO2014120865A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B7/00—Halogens; Halogen acids
    • C01B7/01—Chlorine; Hydrogen chloride
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/38—Separation; Purification; Stabilisation; Use of additives
    • C07C17/389—Separation; Purification; Stabilisation; Use of additives by adsorption on solids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/38—Separation; Purification; Stabilisation; Use of additives
    • C07C17/42—Use of additives, e.g. for stabilisation

Definitions

  • the compound 2,3,3,3-tetrafluoropropene is a low GWP molecule, which can be used as refrigerant, blowing agent, cleaning agent, as well as a monomer of macromolecule compounds.
  • a manufacturing process for 1234yf that uses one of three chlorinated compounds, namely, 1, 1,2,3 -tetra- chloropropene (1230xa), 2,3,3,3-tetrachloropropene (1230xf), and 1,1,1,2,3-pentachloro- propane (240db) as starting raw material, includes the following three steps:
  • Chlorinated compounds such as 1230xa, 1230xf, and 240db, are known to decompose under certain conditions. Those conditions include the presence of air (oxygen), moisture and metal components. While not wishing to be bound to any theory, the present inventors believe that 1230xa, 1230xf, and 240db decomposition occurs due to one or more of the following factors:
  • dimerization of these chlorinated compounds might take place in the presence of metal components, resulting in the formation of dimers (or oligomers) and metallic chlorides.
  • the solution to the decomposition problem of chlorinated compounds including 1230xa, 1230xf and/or 240db as detailed herein comprises the implementation of one or more of the following anti-decomposition techniques which reduce and/or prevent the decomposition of these chlorinated compounds and similar chlorinated compounds that decompose under similar conditions. In certain embodiments, two or more, preferably three or more, and more preferably, all of these techniques are employed. While 1230xa is specifically mentioned below, other chlorinated compounds such as 1230xf, 1230za, trans-1230xd, cis-1230xd, 1240za, 1240zf, 250fb, and 240db, can also be treated in a like manner to reduce and/or prevent decomposition:
  • (5) optionally provide a method and/or device that can remove any HC1 generated during storage and/or transportation.
  • the present invention provides methods for handling, storing and/or transporting 1230xa, and similar reactive chlorinated compounds, whereby decomposition reactions including a purity drop due to conversion to other organic compounds and accelerated corrosion of containers due to HC1 formation are reduced or eliminated by employing one or more of the anti-decomposition techniques selected from the group consisting of: (1) providing a 1230xa supply with little or no moisture, HC1, and/or metallic ions, (2) providing a storage and/or transport tank preferably lined and/or coated with one or more suitable materials, (3) transferring 1230xa, preferably stabilized 1230xa, into a storage and/or transportation tank in such a way that no exposure of the 1230xa to air occurs, (4) handling, storing, and/or transporting 1230xa under the protection of a dried inert gas such as nitrogen, (5) optionally providing a device that can remove any HC1 generated during the storage and/or transportation of 1230xa; and (6) combinations of two or more of these anti-decom
  • One embodiment of the present invention can be generally described as a method for handling, storing, and/or transporting 123 Oxa.
  • Step (1) above thus provides a 1230xa feed supply with little or no moisture, HC1, and/or metallic ions therein.
  • the moisture level is generally lower than 100 ppm, preferably 50 ppm, and more preferably 25 ppm.
  • the HC1 level is generally lower than 200 ppm, preferably 50 ppm, and more preferably 10 ppm.
  • the metallic ion content e.g., iron ion content
  • Various known methods can be used to achieve each of these values.
  • Non-limiting techniques include distillation, and/or absorption using desiccants, and/or the like.
  • Distillation can be operated at atmospheric pressure, super-atmospheric pressure or under vacuum and can be performed using standard distillation methods for separating two compounds.
  • Another method of removing the moisture from 1230xa is by the use of desiccants, whereby the desiccant is in contact with 1230xa for sufficient amount of time to reduce the moisture content.
  • desiccants can be used in a variety of ways, in certain embodiments 1230xa is dried in pre-packaged desiccant in continuous mode.
  • Non-limiting desiccants include silica gel, activated charcoal, calcium sulfate, calcium chloride, montmorillonite clay, and various molecular sieves.
  • the moisture content present in 1230xa is measured by conventional means, such as Karl Fischer titration and the like.
  • HC1 is removed by distillation. Single column or multiple columns may be used. Distillation can be operated at atmospheric pressure, super-atmospheric pressure or under vacuum and can be performed using standard distillation methods for separating two compounds.
  • the amount of HC1 present in 1230xa is determined using standard techniques known in the art. For example, the amount of HC1 present is determined by acid-base titration or IC (Ion Chromatography).
  • any techniques known in the art can be used to remove ionic iron. In one embodiment, it is removed by distillation. Single column or multiple columns may be used. Distillation can be operated at atmospheric pressure, super-atmospheric pressure or under vacuum and can be performed using standard distillation methods for separating two compounds.
  • the amount of ionic iron present in 1230xa is determined using standard techniques known in the art. For example, the amount of iron present is determined by ICP (Inductive Coupled Plasma).
  • Step (2) above thus provides a storage/transport tank preferably lined/coated with suitable materials, Carbon steel, stainless steel and plastic can be used to make the desired storage and/or transport tank.
  • a carbon steel tank internally lined and/or coated with suitable material is preferred.
  • suitable lining and/or coating materials include glass, ceramic, a phenolic or epoxy resin liner such as Plasite 3070 (available from Carboline Company), Plasite 9573 (available from Carboline Company), and Phenicon HS Flake Filled (available from Sherwin Williams), and the like.
  • Yet another embodiment of the present invention can be generally described as a method of transfer of 1230xa such that decomposition is minimized or eliminated.
  • Step (3) above thus provides a method for the transfer of 1230xa, optionally stabilized 1230xa into said storage/transportation tank in such a way that little or no exposure of 1230xa to air occurs.
  • all equipment and the storage and/or transportation tank are subject to an effective purge with a dried inert gas (e.g., nitrogen) to displace air.
  • 1230xa is added with a stabilizer before being transferred or transported.
  • Non-limiting examples include, but are not limited to, diisopropylamine, triethylamine, 4-tert-Amylphenol, 4-methoxyphenol, and their combinations.
  • the amount of stabilizer(s) present in 1230xa can range from about 1 to about 1000 ppm, preferably from about 2 to about 100 ppm, more preferably from about 3 to about 50 ppm, and most preferably from about 4 to about 20 ppm.
  • Another embodiment of the present invention can be generally described as a method of protecting 1230xa such that decomposition is minimized or eliminated. Step
  • Step (4) above is similar to Step (3), wherein the storage and/or transport of 1230xa takes place under the protection of an excess amount of dried nitrogen.
  • the tank is pressurized with dried nitrogen and is then sealed (closed to the atmosphere) to prevent air and/or moisture from entering the tank.
  • Yet another embodiment of the present invention can be generally described as a method of protecting 1230xa such that decomposition is minimized or eliminated. Step
  • Non-limiting solid sorbents include, but are not limited to, alumina, calcium carbonate, sodium carbonate, sodium aluminate, and the like.
  • This example illustrates the effectiveness of 3 A molecular sieves for removing moisture from 1230xa feed.
  • Thel230xa used in Example 1 had a purity of 99.2 GC (gas chromatogram) area% and contained 100 ppm of moisture. 5 ppm of di-isopropyl amine was added into 1230xa as a stabilizer.
  • the 1230xa feed was passed through a 2" ID column loaded with 2 liters of 3 A molecular sieves at rate of 1.0 lb/h and sample was taken from a sampling port after drying column.
  • Moisture level was determined to be 12 ppm by using Mitsubishi Moisture Meter (Model CA-100), indicating 3 A molecular sieve is an effective drying agent for 1230xa.
  • MOC material of construction
  • the materials were carbon steel, stainless steel, and carbon steel coated with Plasite 3070.
  • Four glass tubes were filled with the same amount of solution containing 1230xa and 5 ppm of di-isopropyl amine.
  • Carbon steel, stainless steel, and Plasite 3070 coupons were placed into tube containing solution of 1230xa-di-isopropyl amine and the tubes were then closed.
  • the fourth tube (blank) contained no coupon. All transfers were done under atmosphere of nitrogen. All coupons were 5" long, 1" wide, and 1/8" thick. The tubes were then transferred to an oven kept at 50°C. Periodical visual observations were made and photographs of the tubes were taken.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Engineering & Computer Science (AREA)
  • Mechanical Engineering (AREA)
  • Packages (AREA)

Abstract

La présente invention concerne des procédés pour la manipulation, le stockage et/ou le transport de composés chlorés réactifs tels que du 1230xa permettant la réduction ou l'élimination de réactions de décomposition en utilisant une ou des technique(s) anti-décomposition choisie(s) parmi le groupe constitué de : (a) la fourniture d'un approvisionnement de 1230xa avec peu ou pas d'humidité, de chlorhydrate (HCl), et/ou d'ions métalliques, (b) l'utilisation d'un réservoir de stockage et/ou de transport de préférence doté d'une doublure ou d'un revêtement d'un ou de plusieurs matériau(x) approprié(s), (c) le transfert du 1230xa, de préférence du 1230xa stabilisé, dans un réservoir de stockage et/ou de transport de sorte qu'il ne se produise aucune exposition du 1230xa à l'air, (d) la manipulation, le stockage et/ou le transport du 1230xa sous la protection d'un gaz inerte séché tel que l'azote, (e) l'utilisation éventuelle d'un dispositif pouvant éliminer tout HCl généré pendant le stockage et/ou de transport du 1230xa ; et (f) des combinaisons d'au moins deux de ces techniques anti-décomposition.
PCT/US2014/013742 2013-02-04 2014-01-30 Procédés de manipulation de composés chlorés utilisés dans la fabrication de hfo-1234yf Ceased WO2014120865A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
EP14746383.0A EP2951124A4 (fr) 2013-02-04 2014-01-30 Procédés de manipulation de composés chlorés utilisés dans la fabrication de hfo-1234yf
CN201480007302.XA CN105026311A (zh) 2013-02-04 2014-01-30 处理用于制备hfo-1234yf的含氯化合物的方法
MX2015009943A MX2015009943A (es) 2013-02-04 2014-01-30 Metodos para manejar compuestos clorados utilizados para fabricar el hfo-1234yf.
JP2015556121A JP2016515069A (ja) 2013-02-04 2014-01-30 ＨＦＯ−１２３４ｙｆを製造するために用いる塩素化化合物の取扱方法

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US201361760332P 2013-02-04 2013-02-04
US61/760,332 2013-02-04
US14/165,670 2014-01-28
US14/165,670 US20140215970A1 (en) 2013-02-04 2014-01-28 METHODS OF HANDLING CHLORINATED COMPOUNDS USED FOR MANUFACTURING HFO-1234yf

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Publication Number Publication Date
WO2014120865A1 true WO2014120865A1 (fr) 2014-08-07

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Country Link
US (1) US20140215970A1 (fr)
EP (1) EP2951124A4 (fr)
JP (1) JP2016515069A (fr)
CN (1) CN105026311A (fr)
MX (1) MX2015009943A (fr)
WO (1) WO2014120865A1 (fr)

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US10029962B2 (en) 2015-08-19 2018-07-24 Spolek Pro Chemickou A Hutni Vyrobu A.S. Process for producing C3 chlorinated alkane and alkene compounds
WO2019086816A1 (fr) 2017-11-06 2019-05-09 Arkema France Procede de production de composes fluores

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JP2016519053A (ja) * 2013-03-13 2016-06-30 アーケマ・インコーポレイテッド ヒドロフルオロオレフィンおよびヒドロクロロフルオロオレフィンを精製し、安定化させるための方法
CA3015531A1 (fr) * 2016-03-11 2017-09-14 Blue Cube Ip Llc Procede de stabilisation du chloropropene
FR3049276B1 (fr) * 2016-03-22 2018-03-09 Arkema France Recipient pour le stockage d'une composition comprenant du tetrafluoropropene et methode de stockage de celle-ci

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Publication number Priority date Publication date Assignee Title
US10029962B2 (en) 2015-08-19 2018-07-24 Spolek Pro Chemickou A Hutni Vyrobu A.S. Process for producing C3 chlorinated alkane and alkene compounds
US10851033B2 (en) 2015-08-19 2020-12-01 Spolek Pro Chemickou A Hutni Vyrobu A.S. Process for producing C3 chlorinated alkane and alkene compounds
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WO2019086816A1 (fr) 2017-11-06 2019-05-09 Arkema France Procede de production de composes fluores
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Also Published As

Publication number Publication date
EP2951124A1 (fr) 2015-12-09
MX2015009943A (es) 2015-09-29
JP2016515069A (ja) 2016-05-26
EP2951124A4 (fr) 2016-09-21
US20140215970A1 (en) 2014-08-07
CN105026311A (zh) 2015-11-04

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